Plural Azo Groups Attached Indirectly To Each Other By Nonionic Bonding Patents (Class 534/637)
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Patent number: 5428141Abstract: Reactive dyestuffs which, as the free acid, have the following formula ##STR1## in which K is ##STR2## the bonding to the triazinyl radical taking place in each case via the amino function of K, and the remaining substituents have the meaning given in the description, are suitable in particular for the dyeing and printing of natural and synthetic OH- and/or amido-containing materials.Type: GrantFiled: November 24, 1992Date of Patent: June 27, 1995Assignee: Bayer AktiengesellschaftInventors: Karl-Josef Herd, Thomas Eizenhofer, Wolfgang Harms, Manfred Hoppe, Wolfram Reddig
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Patent number: 5420257Abstract: A reactive dye comprising a 1,3,5-s-triazine group having a chromophoric group at two of the 2-, 4- and 6-positions and a substituent at the remaining 2-, 4- or 6-position selected from H, optionally substituted alkyl, optionally substituted phenyl, --CH(CO.sub.2 R.sup.1).sub.2, --NR.sup.1 SO.sub.2 R.sup.2, and --SO.sub.2 R.sup.2, wherein each R.sup.1 is H or alkyl and R.sup.2 is alkyl. The reactive dyes may be used for the coloration of textile materials.Type: GrantFiled: September 17, 1993Date of Patent: May 30, 1995Assignee: Zeneca LimitedInventors: Kenneth Anderton, Andrew P. Shawcross
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Patent number: 5420255Abstract: A process for the continuous reaction of halogenopyrimidines with amines, a halogenopyrimidine and an aqueous amine solution or suspension being passed into a reactor and the reaction product being subsequently conducted away, is described, characterized in that the starting materials are introduced into the reactor simultaneously and continuously with intensive mixing.Type: GrantFiled: February 22, 1994Date of Patent: May 30, 1995Assignee: Bayer AktiengesellschaftInventors: Siegbert Arnold, Hans-Georg Frosch, Manfred Hoppe, Wolfgang Mullers, Richard Sommer
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Patent number: 5420256Abstract: Reactive dyestuffs have the following formula ##STR1## in which D is the radical of an organic dyestuffB is a direct bond or a bridging member on a ring C atom of an aromatic-carbocyclic or on a ring C atom or N atom of an aromatic-heterocyclic ring in D,R.sub.a, R.sub.b, identical or different, are H, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkyl substituted by OH, CN, CO.sub.2 H, OSO.sub.3 H or SO.sub.3 H,U is Cl, F or a pyridinium radical which is unsubstituted or substituted by CO.sub.2 H, CONH.sub.2, SO.sub.3 H or C.sub.1 -C.sub.4 -alkyl,W is straight-chain or branched C.sub.1 -C.sub.6 -alkylene,Y is CH.dbd.CH.sub.2 or CH.sub.2 --CH.sub.2 --X, in whichX is a radical which can be eliminated by alkali,V is H, halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.3 -alkyl, CN, COOH, CONH.sub.2, SO.sub.3 H.Type: GrantFiled: January 27, 1993Date of Patent: May 30, 1995Assignee: Bayer AktiengesellschaftInventors: Thomas Eizenhofer, Wolfgang Harms, Karl-Josef Herd
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Patent number: 5405415Abstract: Water-soluble fiber-reactive disazo compounds of the formula (1) given and defined below are described, which compounds serve as dyes for dyeing and printing hydroxy- and/or carboxamido-containing material, in particular fiber material, such as wool and synthetic polyamide and, in particular, cellulose fiber materials, such as cotton. ##STR1## In this formula M is hydrogen or an alkali metal, the groups Y--SO.sub.2 -- and --SO.sub.2 --Y.sup.0 are fiber-reactive groups from the vinylsulfone series, m is 1 or 2, n is zero or 1, R is a group of the formula (2) or (3) ##STR2## in which R.sup.A is lower alkyl which may be substituted, or is phenyl which may be substituted by sulfo, carboxy, lower alkyl and/or lower alkoxy, X is chlorine, fluorine, hydroxy, alkoxy, cycloalkoxy or alkoxy of 3 to 8 carbon atoms whose alkyl radical is interrupted by --O--, --NH--, --CO--NH-- or --NH--CO--, or is benzyloxy, sulfomethoxy, .beta.Type: GrantFiled: June 23, 1994Date of Patent: April 11, 1995Assignee: Hoechst AGInventors: Uwe Reiher, Werner H. Russ
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Patent number: 5403920Abstract: Reactive dyes of the formula ##STR1## in which A, U, R.sub.1, R.sub.2, Z and n are as defined in claim 1, are particularly suitable for dyeing or printing cellulosic fibre materials or naturally occurring or synthetic polyamide fibre materials with a high tinctorial yield and produce dyeings and prints with good fastness properties.Type: GrantFiled: July 19, 1993Date of Patent: April 4, 1995Assignee: Ciba-Geigy CorporationInventors: Herbert Klier, Athanassios Tzikas
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Patent number: 5399674Abstract: Fiber-reactive dyestuffs, processes for their preparation and their useDyestuffs of the formula (1) are described ##STR1## The dyestuffs have fiber-reactive properties and dye materials containing hydroxy groups and/or containing carboxamide groups, in particular fiber materials, such as, for example, cellulose fibers, wool and synthetic polyamide fibers, in deep, fast shades by the methods known for this process.Type: GrantFiled: December 3, 1993Date of Patent: March 21, 1995Assignee: Hoechst AktiengesellschaftInventors: Jorg Dannheim, Werner H. Russ
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Patent number: 5391718Abstract: Reactive dyes of the formula ##STR1## in which K and Z are as defined in the disclosure, are suitable in particular for the dyeing and printing of cellulose-containing fibre material and produce dyeings and prints having good fastness properties in high coloristic yield.Type: GrantFiled: February 26, 1993Date of Patent: February 21, 1995Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Claudia Carisch
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Patent number: 5386015Abstract: Compounds of the formula ##STR1## and salts thereof, and mixtures of such compounds and salts, wherein F.sub.c is ##STR2## wherein D.sub.1 is an unsubstituted or substituted phenyl or naphthyl diazo component radical,each of Q.sub.1, Q.sub.2 and Q.sub.3 is independently hydrogen or a substituent,each R.sub.5 is independently hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,each R.sub.6 is independently hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, (C.sub.1-4 alkyl)carbonylamino or --NH--CO--NH.sub.2,R.sub.16 is hydrogen or --SO.sub.3 H,r is 1 or 2, andt is 2 or 3, andb is 1 or 2,whereineach R.sub.1 is independently hydrogen or C.sub.1-4 alkyl,each R.sub.7 is independently hydroxy, C.sub.1-4 alkoxy or --NH.sub.2,each Z is independently ##STR3## and each m is independently 0 or 1.Type: GrantFiled: July 9, 1993Date of Patent: January 31, 1995Assignee: Sandoz Ltd.Inventors: Paul Doswald, Werner Koch
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Patent number: 5378817Abstract: Reactive dyestuffs of the formula ##STR1## wherein Z=a heterocyclic reactive group and the remaining groups have the meaning given in the description, are outstandingly suitable for dyeing and printing materials containing hydroxyl groups or amide groups.Type: GrantFiled: January 15, 1993Date of Patent: January 3, 1995Assignee: Bayer AktiengesellschaftInventors: Konrad Bootz, Karl-Josef Herd
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Patent number: 5374301Abstract: An ink comprising a liquid medium and a compound of Formula (1) or salt thereof: ##STR1## provided (i) if the compound of Formula (1) has no --SO.sub.3 H groups then it has at least two groups selected from --COOH and --COSH; and (ii) the compound of Formula (1) has at least as many groups selected from --COOH and --COSH as --SO.sub.3 H groups. The inks are useful for ink-jet printing.Type: GrantFiled: November 30, 1992Date of Patent: December 20, 1994Assignee: Zeneca LimitedInventors: Peter Gregory, Ronald W. Kenyon
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Patent number: 5359043Abstract: A water soluble dye having a reactive group of the formula: ##STR1## wherein: T is a labile atom or group; andR.sup.2 and R.sup.3 are each independently a non-chromophoric optionally substituted aryl or alkyl group.Type: GrantFiled: April 21, 1992Date of Patent: October 25, 1994Assignee: Zeneca LimitedInventors: Stephen B. Bostock, Michael G. Hutchings, John A. Taylor
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Patent number: 5359042Abstract: New reactive dyestuffs which, in the form of the free acid, correspond to the following formula ##STR1## wherein the substituents have the meaning given in the description, are suitable for dyeing and printing materials containing hydroxyl groups or amide groups, in particular cellulose materials.Type: GrantFiled: April 29, 1993Date of Patent: October 25, 1994Assignee: Bayer AktiengesellschaftInventors: Horst Jager, Frank-Michael Stohr
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Patent number: 5354849Abstract: Anionic disazo compounds of the formula ##STR1## and salts thereof each cation of which is independently a non-chromophoric cation, and mixtures of such compounds or salts, wherein D is whereinR.sub.4 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or halo,R.sub.1 is hydrogen, C.sub.1-4 alkyl or C.sub.2-4 hydroxyalkyl,R.sub.2 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, (C.sub.1-4 alkyl)carbonylamino, (C.sub.1-4 alkoxy)carbonylamino or --NHCONH.sub.2,R.sub.3 is hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, and ##STR2## wherein R.sub.5 is chloro, hydroxy or --NHCN,R.sub.6 is hydrogen, chloro or cyano, andR.sub.7 and R.sub.8 are as defined in the specification, with the proviso that R.sub.7 and R.sub.8 together contain at least 8 carbon atoms,useful for dyeing or printing anionically dyeable organic substrates such as nitrogen-containing substrates, particularly fiber material comprising natural or synthetic polyamide.Type: GrantFiled: June 4, 1993Date of Patent: October 11, 1994Assignee: Sandoz Ltd.Inventor: Georg Schoefberger
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Patent number: 5354850Abstract: Water-soluble disazo compounds, a process for their preparation and their use as dyes.Disazo compounds are described which have the formula (1) given and defined below and are used in their function as fiber-reactive dyes for the dyeing of hydroxy- and/or carboxamido-containing fiber material, such as cellulose fiber materials and synthetic and natural polyamide fiber materials, such as wool. They produce brown dyeings and prints having high color strength and good color fastness by the application and fixation methods customary for fiber-reactive dyes ##STR1## in which R is hydrogen or sulfo,R.sup.1 is hydroxy, methoxy or ethoxy,is hydrogen or an alkali metal and the non-fixed sulfo group in the naphthylene radical is in the 6 or 7 position.Type: GrantFiled: June 24, 1993Date of Patent: October 11, 1994Assignee: Hoechst AGInventors: Andreas von der Eltz, Werner H. Russ
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Patent number: 5349057Abstract: Water-soluble azo dyes and their heavy metal complex derivatives, such as copper, cobalt and chromium complex azo dyes are described, which have the general formula (1) shown below, have fiber-reactive properties and dye natural and synthetic hydroxyl- and/or carboxamido-containing materials, in particular fiber materials, such as wool and in particular cellulose fiber materials, by the dyeing and printing processes customary for fiber-reactive dyes, in hues which have high color strength and good fastness properties.Type: GrantFiled: January 10, 1992Date of Patent: September 20, 1994Assignee: Hoechst AktiengesellschaftInventors: Holger M. Buch, Hartmut Springer
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Patent number: 5328995Abstract: The compounds of the formula ##STR1## where the substituents are as defined in claim 1, are direct dyes for various substrates, in particular cellulosic fibre materials. They are high temperature resistant and therefore are particularly highly suitable for the one-bath, single-stage dyeing of polyester/cotton blend fabrics with a disperse dye for the polyester fibres under the dyeing conditions for polyester fibres.Type: GrantFiled: January 27, 1993Date of Patent: July 12, 1994Assignee: Ciba-Geigy CorporationInventors: Rudolf Schaulin, Urs Lauk
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Patent number: 5319074Abstract: A metal-free dyestuff of the formula ##STR1## and metal complex thereof wherein: Fb=the radical of a dyestuff selected from the group consisting of mono- or polyazo, anthraquinone, phthalocyanine, formazan, dioxazine and triphenylmethane radicals,B and B'=a direct bond or an aliphatic or aromatic bridge member to a ring C atom of an aromatic-carbocyclic ring or to a ring C or N atom or an aromatic-heterocyclic ring in Fb,X=CH.dbd.CH.sub.2 or CH.sub.2 CH.sub.2 --Y, whereinY=OSO.sub.3 H, SSO.sub.3 H, OCOCH.sub.3, OPO.sub.3 H.sub.2, OSO.sub.2 CH.sub.3, SCN, NHSO.sub.2 CH.sub.3 --, Cl, Br, F, OCOC.sub.6 H.sub.5, OSO.sub.2 --C.sub.6 H.sub.4 CH.sub.3, ##STR2## R=H or C.sub.1 -C.sub.4 -alkyl, which is optionally be substituted by halogen, hydroxy, cyano, C.sub.1 -C.sub.4 -alkoxy, carboxyl, sulpho or sulphato,Z=a fiber-reactive radical of the formula ##STR3## wherein M=H, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -thioalkyl, F or CF.sub.Type: GrantFiled: January 24, 1992Date of Patent: June 7, 1994Assignee: Bayer AktiengesellschaftInventors: Wolfram Reddig, Karl-Josef Herd, Ernst Kysela
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Patent number: 5310886Abstract: There are disclosed azo compounds conforming to formula (1) shown and defined hereinafter, and the preparation thereof. They have fiber-reactive properties and are used for preparing strong and fast dyeings on hydroxy- and/or carboxamido-containing material, preferably fiber material, such as synthetic polyamide, wool and in particular cellulose fibers. ##STR1## where: M is hydrogen or a salt-forming metal,K.sup.o is a radical of the formula (2A) or (2B) ##STR2## where Z is a radical of the formula (3) ##STR3## where R.sup.o is hydrogen or lower alkyl which may be substituted by certain substituents, G is halogen, methoxy, hydroxy or substituted or unsubstituted anilino, Z.sup.1 is a radical of the formula (3a) or (3b) ##STR4##--alk--SO.sub.2 --Yand wherein A, B, R*, R", Y, a, k, D, E and K are as defined in the specification.Type: GrantFiled: June 25, 1992Date of Patent: May 10, 1994Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Kurt Hussong
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Patent number: 5306814Abstract: A bisazo compound represented by the following formula (I) in the free acid form: ##STR1## wherein R is hydrogen or unsubstituted or substituted C.sub.1 -C.sub.4 alkyl; A is an unsubstituted or substituted phenylene or naphthylene group; Z is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Y, in which Y is a group capable of being split by the action of an alkali; X is --NR.sub.1 R.sub.2, C.sub.5 -C.sub.7 cycloalkylamino or ##STR2## in which Q is --CH.sub.2 --, --O--, --SO.sub.2 --, --SO-- or --NR.sub.3 -- in which R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; and n is 1 or 2; R.sub.1 is hydrogen or unsubstituted or substituted alkyl; R.sub.Type: GrantFiled: December 17, 1992Date of Patent: April 26, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Kingo Akahori, Takeshi Washimi, Takashi Omura, Mahito Fujita
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Patent number: 5300633Abstract: Azo compounds of the formula D.sup.o --N.dbd.N--K.sup.o, in which D.sup.o is a radical of the formula (2), (2a) or (2b) ##STR1## in which Y is a substituent which can be eliminated by alkali to form the vinyl group, X is chlorine or bromine and R is hydrogen, lower alkyl, phenyl or halogen, and K.sup.o is the radical of a coupling component or another radical which contains azo groups, K.sup.o containing a group of the formula --N(R.sup.o)--Z, in which R.sup.o is hydrogen or lower alkyl and Z is a radical of the formula ##STR2## in which A is halogen or cyanoamido, R.sup.20 is hydrogen or lower alkyl, and R.sup.21 has one of the meanings given for R.sup.20, or is an optionally methyl-substituted cycloalkylene radical, or is a phenyl radical, or in which R.sup.20 and R.sup.21, together with the nitrogen atom and if appropriate one or two further hetero groups, can form a 5- or 6-membered heterocyclic radical.Type: GrantFiled: May 8, 1992Date of Patent: April 5, 1994Assignee: Hoechst AktiengesellschaftInventors: Jorg Dannheim, Werner H. Russ
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Patent number: 5298607Abstract: The invention provides reactive dyes of the formula ##STR1## wherein D is a mono- or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, dioxazine or stilbene dye which contains sulfo groups, R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, methyl or ethyl, X is a radical of the formula --SO.sub.2 CH.sub.2 CH.sub.2 Cl, --SO.sub.2 CH.dbd.CH.sub.2, --SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, --SO.sub.2 CH.sub.2 CH.sub.2 OPO.sub.3 H or --N(R.sub.3)SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, and R.sub.3 is hydrogen, methyl or ethyl, and the benzene or naphthalene radical is not further substituted or is further substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.Type: GrantFiled: May 26, 1993Date of Patent: March 29, 1994Assignee: Ciba-Geigy CorporationInventor: Herbert Seiler
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Patent number: 5290922Abstract: Disazo compounds which possess fiber-reactive groups and have useful dye properties and are capable of dyeing hydroxyl- and/or carboxamido-containing materials, in particular fiber materials, such as cellulose fibers and natural and synthetic polyamide, such as wool, in strong, fast shades. They conform to the formula ##STR1## wherein the substituents are as defined in the specification.Type: GrantFiled: December 30, 1992Date of Patent: March 1, 1994Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Rolf Gleibner
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Patent number: 5276148Abstract: Reactive dyes of the formula ##STR1## where n is 0 or 1,R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,A is unsubstituted or substituted C.sub.2 -C.sub.8 -alkylene,Y is vinyl or a radical of the formula --CH.sub.2 --CH.sub.2 --Q, whereQ is a group which can be eliminated under alkaline reaction conditions,D.sup.1 is phenyl or naphthyl, where these radicals may be substituted,D.sup.2 is phenylene or naphthylene, where these radicals may be substituted, andZ is a reactive radical,with the proviso thata) n is zero when D.sup.1 is substituted by unsubstituted or substituted phenylazo or by unsubstituted or substituted naphthylazo andb) the reactive radical Z is not devised from the triazine series when n is zero and D.sup.1 is dihydroxysulfonylphenyl or trihydroxysulfonylnaphthyl,are used for dyeing and printing organic substrates containing hydroxyl groups or nitrogen atoms.Type: GrantFiled: May 22, 1992Date of Patent: January 4, 1994Assignee: BASF AktiengesellschaftInventors: Bernd Siegel, Manfred Patsch
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Patent number: 5268459Abstract: Anionic azo compounds which, in the free acid form, have the Formula (1): ##STR1## wherein: Ar and Ar.sup.1 are each independently aryl or substituted aryl providing at least one of Ar and Ar.sup.1 has at least one substituent selected from COOH and COSH;J and J.sup.1 are each independently of formula (2), (3) or (4): ##STR2## each R.sup.5 is independently selected from H, alkyl, substituted alkyl, alkoxy, halogen, CN, ureido and NHCOR.sup.6 ;R.sup.6 is H, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl or substituted aralkyl;each T is independently alkyl;each W is independently selected from H, CN, CONR.sup.10 R.sup.11, pyridinium and COOH;each m is an alkylene chain having 2 to 8 carbon atoms;B is H, alkyl or COOH;R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.10 and R.sup.11 are each independently H, alkyl or substituted alkyl;L is a divalent organic linking group;n is 0 or 1;each X is independently carbonyl or a group of the Formula (5), (6) or (7): ##STR3## Z is OR.sup.7, SR.sup.7 or NR.sup.8 R.sup.Type: GrantFiled: June 28, 1991Date of Patent: December 7, 1993Assignee: Imperial Chemical Industries plcInventors: Peter Gregory, Ronald W. Kenyon
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Patent number: 5268457Abstract: Reactive dyes of the formula ##STR1## are particularly suitable for dyeing or printing cellulosic fibre materials by the exhaust method or by continuous processes and give, with a high color yield, dyeings and prints with good fastness properties, in which D is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye; R is hydrogen or alkyl having 1 to 4 carbon atoms, which can be substituted by hydroxyl, cyano, carboxyl, sulfo or sulfato; X is fluorine or chlorine; B is a substituted or unsubstituted aliphatic or aromatic bridge member; Y is a substituted or unsubstituted aliphatic, aromatic, araliphatic or heterocyclic radical, which is free from reactive groups; R.sub.2 is hydrogen or alkyl having 1 to 4 carbon atoms, which can be substituted by halogen, hydroxyl, cyano, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.Type: GrantFiled: December 28, 1992Date of Patent: December 7, 1993Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
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Patent number: 5268458Abstract: Azo compounds containing, as the diazo constituent, 1-sulpho-6-carboxy-2-aminonaphthalene and, as the coupling constituent, substances which contain a residue of the pyrimidine or triazine series which reacts with fibers. The azo compounds possess dye properties and, when used in the usual application fixing process for fiber-reactive dyes, color materials containing carbonamide and/or hydroxyl groups, in particular fibrous material such as wool, synthetic nylon and, in particular, cellulose fiber materials in intense, permanent shades.Type: GrantFiled: June 25, 1992Date of Patent: December 7, 1993Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Kurt Hussong
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Patent number: 5256774Abstract: Improved reactive dyestuffs have the following formula ##STR1## in which the substituents have the meaning given in the description.Type: GrantFiled: February 20, 1992Date of Patent: October 26, 1993Assignee: Bayer AktiengesellschaftInventors: Wolfgang Harms, Thomas Eizenhofer
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Patent number: 5243033Abstract: Reactive dyes of the formula ##STR1## in which R.sub.1, R.sub.2 and R.sub.3, independently of one another, are C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, ureido, C.sub.1 -C.sub.4 acylamino, carboxyl and sulfo and n, m and p, independently of one another, are the number 0, 1, 2 or 3, X is fluorine or chorine and Z is an aliphatic, araliphatic, aromatic or heterocyclic amino group free from fibre-reactive radicals; or Z is the radical of an aliphatic or aromatic diamine which contains the radical of the formula ##STR2## in which R.sub.1, R.sub.2, R.sub.3, n, m, p and X are as defined, bound via the second amino group; or Z is a radical of the formula ##STR3## in which R.sub.1, R.sub.2, R.sub.3, n, m, and p are as defined; or Z is a radical --NH--SO.sub.2 --(CH.sub.2).sub.2 --OSO.sub.3 H; and the reactive dye of the formula (1) contains at least two sulfo groups, produce, on cellulose fibres, orange dyeings of high color strength and prints of good fastness properties.Type: GrantFiled: January 13, 1992Date of Patent: September 7, 1993Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
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Patent number: 5243034Abstract: Disazo dyestuffs containing sulfo groups and having fiber-reactive properties, which are capable of dyeing materials containing hydroxyl groups and/or carboxamide groups, in particular fiber materials, such as synthetic polyamide fibers, wool and in particular cellulose fiber materials, in deep fast shades. They contain a group corresponding to the formula ##STR1## in which R.sup..alpha. is hydrogen or alkyl having 1 to 4 carbon atoms, which can be substituted by carboxyl, sulfo, cyano, hydroxyl or chlorine;B is fluorine, chlorine, bromine, lower alkylsulfonyl, phenylsulfonyl, methoxy or sulfo;Q is a group of the formula ##STR2## in which Y is vinyl, .beta.-sulfatoethyl, .beta.-halogenoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl or .beta.-acetoxyethyl,R is hydrogen or lower alkyl,k is the number zero to 4 andX, together with the N atom, forms the bivalent radical of a heterocyclic ring which optionally contains additional hetero atoms.Type: GrantFiled: November 18, 1991Date of Patent: September 7, 1993Assignee: Hoechst AktiengesellschaftInventors: Horst Tappe, Dieter Oehme, Holger M. Buch, Werner H. Russ
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Patent number: 5241057Abstract: Dyestuffs of the formula ##STR1## wherein X=--CH.dbd.CH.sub.2, --CH.sub.2 --CH.sub.2 OSO.sub.3 H, --CH.dbd.CHCl or --CH.sub.2 --CH.sub.2 Cl andY=a fiber-reactive fluoropyrimidinyl or fluorotriazine radical andwhereinu and v=H or SO.sub.3 H, where u.apprxeq.v. Such dyestuffs suitable for dyeing and printing diverse substrates, particularly cotton, to give products a high degree of dyestuff fixation.Type: GrantFiled: November 1, 1991Date of Patent: August 31, 1993Assignee: Bayer AktiengesellshaftInventor: Horst Jager
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Patent number: 5233026Abstract: Reactive dyes of the formula ##STR1## in which D is a monoazo dye, R.sub.1 is hydrogen or a substituted or unsubstituted C.sub.1-4 alkyl radical, Z is an unsubstituted or substituted amino group, and X is a vinyl, .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-chloroethyl or .beta.-acetoxyethyl group, with the condition that Z is not a sulfo- or carboxyl-substituted phenylamino group when the triazine radical is bonded to the radical of 1,8-aminonaphthol-3,6- or -4,6-disulfonic acid, and the X--SO.sub.2 radical is bonded directly to an aromatic C atom, are suitable in particular for dyeing and printing cellulose-containing fiber materials by the cold pad-batch method and produce, in high dyeing yields, dyeings and prints having good fastness properties.Type: GrantFiled: August 2, 1991Date of Patent: August 3, 1993Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
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Patent number: 5231171Abstract: Reactive dyes useful for dyeing or printing hydroxyl- or nitrogen-containing substrates have the formula ##STR1## where Rg is a radical of the formula ##STR2## Ar is the radical of a benzene or naphthalene ring, Z.sup.1 and Z.sup.2 are each hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, substituted or unsubstituted phenyl, C.sub.1 -C.sub.4 -alkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, cyano, halogen or hydroxysulfonyl,Z.sup.3, Z.sup.4 and Z.sup.5 are each hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or substituted or unsubstituted phenyl,U is a group which is detachable under alkaline reaction conditions,X is in case a) the radical of a chromophore or in case b) the radical of a coupling component to which may additionally be attached, via an azo bridge, the radical of a diazo component and which may have additional reactive groups, andL is in case a) a bridge member or in case b) an azo bridge.Type: GrantFiled: December 13, 1991Date of Patent: July 27, 1993Assignee: BASF AktiengesellschaftInventors: Claus Marschner, Matthias Niedenbrueck, Bernd Siegel, Manfred Patsch, Klaus Pandl
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Patent number: 5210187Abstract: Double attachment reactive dyes have the formula ##STR1## where U.sup.1 is C.sub.1 -C.sub.4 -alkyl, phenyl, C.sub.2 -C.sub.10 -alkenyl or the radical ##STR2## where Q.sup.1 and Q.sup.2 are each independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl and Q.sup.3 is a group which is detachable under alkaline reaction conditions,Z is the radical ##STR3## where each Q.sup.4 is independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl which may be substituted by cyano, U.sup.2 is C.sub.1 -C.sub.4 -alkyl, phenyl, C.sub.2 -C.sub.10 -alkenyl or the radical ##STR4## where Q.sup.5 and Q.sup.6 are each independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl and Q.sup.7 is a group which is detachable under alkaline reaction conditions, and w is 0, 1 or 2,t is 0, 1 or 2,v is 1 or 2 and X and L are each as defined in the description, with the proviso that at least one of the two radicals U.sup.1 and U.sup.2 is not C.sub.1 -C.sub.Type: GrantFiled: April 9, 1992Date of Patent: May 11, 1993Assignee: BASF AktiengesellschaftInventors: Manfred Patsch, Uwe Nahr, Friedrich Wirsing, Joerg L. Jessen, Klaus Pandl, Claus Marschner, Matthias Dust
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Patent number: 5200511Abstract: Reactive dyes of the formula ##STR1## where m is 0 or 1,A.sup.1 and A.sup.2 are different and each is a fiber-reactive radical or else, in the case of A.sup.2, hydrogen,D.sup.1 and D.sup.2 are substituted or unsubstituted phenylene, substituted or unsubstituted phenylenemethyl, substituted or unsubstituted naphthylene or substituted or unsubstituted naphthylenemethyl,K.sup.1 and K.sup.2 are each the radical of a coupling component of the aminonaphthalenesulfonic acid series andL is a bridge member,are useful for dyeing and printing hydroxyl- or nitrogen-containing substrates.Type: GrantFiled: March 30, 1992Date of Patent: April 6, 1993Assignee: Basf AktiengesellschaftInventors: Hermann Loeffler, Manfred Patsch
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Patent number: 5197992Abstract: A water-soluble reactive dye of the formula:D.sup.1 --Z.sup.1 --NR.sup.1 --T--NR.sup.2 --Z.sup.2 --D.sup.2 (1)whereineach of D.sup.1 and D.sup.2, independently, represents the radical of a water-soluble chromophoric compound,each of Z.sup.1 and Z.sup.2, independently, represents a triazine or pyrimidine residue carrying an atom or group imparting fibre-reactivity to the dye,R.sup.1 represents an optionally substituted alkyl radical,R.sup.2 represents hydrogen or an optionally substituted alkyl radical, andT represents a 1,3- or 1,4-phenylene radical which may carry one or more substituents selected from halogen, alkyl, alkoxy, acylamino, nitro and carboxy.Type: GrantFiled: January 30, 1991Date of Patent: March 30, 1993Assignee: Imperial Chemical Industries PLCInventors: John A. Taylor, Duncan A. S. Phillips, Chu K. Yung, Gerard Ellis
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Patent number: 5196033Abstract: A water-soluble reactive dye of the formula:D.sup.1 --Z.sup.1 --NR.sup.1 --T--NR.sup.2 --Z.sup.2 --D.sup.2 (1)whereineach of D.sup.1 and D.sup.2, independently, represents the radical of a water-soluble chromophoric compound,each of Z.sup.1 and Z.sup.2, independently, represents a triazine or pyrimidine residue carrying an atom or group imparting fibre-reactivity to the dye,R.sup.1 represents an optionally substituted alkyl radical,R.sup.2 represents hydrogen or an optionally substituted alkyl radical, andT represents a 1,3- or 1,4-phenylene radical which may carry one or more substitutents selected from halogen, alkyl, alkoxy, acylamino, nitro and carboxy.Type: GrantFiled: July 9, 1991Date of Patent: March 23, 1993Assignee: Imperial Chemical Industries plcInventor: John A. Taylor
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Patent number: 5182371Abstract: The reactive dyes have the formula ##STR1## where n is 0 or 1,R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,R.sup.4 is fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl or a radical of the formula ##STR2## L is a bridgemember, A is substituted or unsubstituted C.sub.2 -C.sub.8 -alkylene,Y is vinyl or a radical of the formula --CH.sub.2 --CH.sub.2 --Q, where Q is a group which is detachable under alkaline reaction conditions, andD is phenyl or naphthyl, which may each be substituted.The present dyes are useful in dyeing or printing hydroxyl- or nitrogen-containing fibres.Type: GrantFiled: February 14, 1992Date of Patent: January 26, 1993Assignee: BASF AktiengesellschaftInventors: Bernd Siegel, Manfred Patsch
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Patent number: 5175260Abstract: Disazo dyes suitable for preparing inks have the formula ##STR1## where m is 1 or 2,n is 0 or 1,Z.sup.1 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl,Z.sup.2 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkanoyl, substituted or unsubstituted benzoyl, C.sub.1 -C.sub.4 -alkylsulfonyl, substituted or unsubstituted phenylsulfonyl or a derivatized 1,3,5-triazinyl radical, andD is the radical of a diazo component of the class of the thiazole, thiophene, aminobenzoic acid or phenylenediamine compounds.Type: GrantFiled: August 8, 1991Date of Patent: December 29, 1992Assignee: BASF AktiengesellschaftInventors: Gunter-Rudolf Schroeder, Udo Mayer
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Patent number: 5166325Abstract: The new polyazo reactive dyestuffs of the formula ##STR1## in which the substituents have the meaning given in the description are highly suitable for the dyeing or printing of hydroxyl- or amido-containing materials. The dyeings and prints obtained are distinguished by high fibre-dyestuff bonding stability and by particularly good stability to oxidizing agents.Type: GrantFiled: April 25, 1991Date of Patent: November 24, 1992Assignee: Bayer AktiengesellschaftInventors: Karl-Josef Herd, Hermann Henk, Karl-Heinz Schundehutte, Frank-Michael Stohr
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Patent number: 5118737Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein R.sup.1 is --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H,R.sup.2 is H or --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H, orR.sup.1 and R.sup.2 together with the nitrogen atom form a morpholine ringa and b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;M is H, ammonium, or a monovalent metal;X (i) NR.sup.1 R.sup.2, (ii) NR.sup.3 R.sup.4, in which R.sup.3 and R.sup.Type: GrantFiled: June 22, 1990Date of Patent: June 2, 1992Assignee: Canon Kabushiki KaishaInventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
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Patent number: 5116956Abstract: A polyazo compound of the following formula, ##STR1## wherein X is ##STR2## --NR.sub.2 R.sub.3, --OR.sub.4 or --SR.sub.5, in which R.sub.1 is hydrogen or alkyl, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each hydrogen, alkyl, phenyl, naphthyl or benzyl, A is phenylene, naphthylene or alkylene, Z is a fiber-reactive group of --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z' in which Z' is a splittable group, Y is pyridinio, and F is polyazo dye moiety carrying a fiber-reactive group like that represented by Z, which compound is useful for dyeing or printing fiber materials to obtain a product dyed or printed in a color superior in various fastness properties with superior build-up property.Type: GrantFiled: May 17, 1990Date of Patent: May 26, 1992Assignee: Sumitomo Chemical Co., Ltd.Inventors: Tetsuya Miyamoto, Kazufumi Yokogawa, Yutaka Kayane, Takashi Omura, Takeshi Washimi, Naoki Harada, Kingo Akahori
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Patent number: 5112959Abstract: A polyazo compound of the following formula, ##STR1## wherein A is phenylene, naphthylene or alkylene, X is --NR.sub.2 R.sub.3, --OR.sub.4 or --SR.sub.5 in which R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each hydrogen, alkyl, phenyl, naphthylene or benzyl, Z is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z' in which Z' is a splittable group, R.sub.1 is hydrogen or alkyl, and F is polyazo dye moiety carrying a fiber reactive group like that represented by Z. This compound is useful for the dyeing or printing of fiber materials to obtain a product dyed or printed in a color superior in various fastness properties with superior build-up property.Type: GrantFiled: May 22, 1990Date of Patent: May 12, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Tetsuya Miyamoto, Kazufumi Yokogawa, Yutaka Kayane, Takashi Omura, Takeshi Washimi, Naoki Harada, Kingo Akahori
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Patent number: 5091515Abstract: A new process for the preparation of substituted 2,4-diamino-6-flurotriazines of the formula ##STR1## in which the substituents have the meanings given in the description, comprises reacting ammonium salts of the formula ##STR2## in an aqueous medium at pH values of about 2.5-10 with 2,4,6-trifluorotriazine in a continuous process. The reaction products can be converted to dyestuffs without isolating the intermediates.Type: GrantFiled: May 3, 1990Date of Patent: February 25, 1992Assignee: Bayer AktiengesellschaftInventors: Karl J. Herd, Hans-Georg Frosch, Hermann Henk, Wolfgang Mullers, Frank-Michael Stohr
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Patent number: 5079347Abstract: Disazo compounds conforming to a general formula (1) shown below which have fiber-reactive dye properties and dye hydroxy- and/or carboxamido-containing fiber materials, such as wool and in particular cellulose, in strong fast shades. ##STR1## where R is a hydrogen atom or a sulfo group,R.sup.1 is a hydroxy group, a methoxy group or an ethoxy group,M is a hydrogen atom or an alkali metal,X is a chlorine atom or a fluorine atom,Y is a chlorine atom or an amino group or a group of the general formula (2) ##STR2## where R* is a hydrogen atom or a methyl or ethyl group,n is zero, 1 or 2,R.sup.2 is a hydrogen atom or a sulfo group or a .beta.-sulfatoethylsulfonyl group or a vinylsulfonyl group, andR.sup.3 is a sulfo group or a .beta.-sulfatoethylsulfonyl group or a vinylsulfonyl group,it being possible for R.sup.2 and R.sup.3 to be identical to or different from each other.Type: GrantFiled: December 6, 1988Date of Patent: January 7, 1992Assignee: Hoechst AktiengesellschaftInventor: Holger M. Buch
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Patent number: 5075428Abstract: A dyestuff of the formula ##STR1## in which R is H or Ch.sub.3 ##STR2## in which R.sub.1 is H, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or --X--YX is a divalent aliphatic, cycloaliphatic, aliphaticcycloaliphatic radical or an araliphatic radicalY is COOH, SO.sub.3 H, OSO.sub.3 H or SO.sub.2 G, in whichG is CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --Z, in which Z denotes a group which can be eliminated under alkaline conditions,R.sub.2 is H or C.sub.1 -C.sub.4 -alkyl, and the benzene radical D and the benzene or naphthalene radical L can contain customary substituents,is suitable for the dyeing and printing of OH- and NH-containing materials. They produce lightfast and wetfast brilliant dyeings and prints.Type: GrantFiled: July 11, 1989Date of Patent: December 24, 1991Assignee: Bayer AktiengesellschaftInventor: Horst Jager
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Patent number: 5047514Abstract: Reactive dyes which contain at least one radical of the formula--SO.sub.2 --CH.dbd.CH.sub.2 (1a)or--SO.sub.2 --CH.sub.2 CH.sub.2 --X (1b)and at least one radical of the formula ##STR1## in which X is an inorganic or organic radical detachable under alkaline conditions, R is hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl, Y is oxygen or sulfur and R.sub.1 is a substituted or unsubstituted aliphatic radical, give dyeings or prints having good fastness properties.Type: GrantFiled: November 5, 1987Date of Patent: September 10, 1991Assignee: Ciba-Geigy CorporationInventors: Peter Scheibli, Karl Seitz
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Patent number: 5021558Abstract: Water-soluble fiber-reactive azo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylemthane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dyes which contain once or twice the group of the general formula ##STR1## in which: R.sup.x and R.sup.z are, independently of one another, hydrogen or lower alkyl, which can be substituted by halogen, hydroxyl, cyano, lower alkoxy, lower alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato;W is fluorine, chlorine, bromine, sulfo, phenylsulfonyl or alkylsulfonyl of 1 to 4 carbon atoms;Y is vinyl, .beta.-substituted, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-alkanoyloxyethyl of 2 to 5 carbon atoms in the alkanoyl radical, .beta.-benozoyloxyethyl, .beta.-(sulfobenzoyloxy)ethyl, .beta.-(p-toluenesulfonyloxy)ethyl or .beta.-halogenoethyl.Type: GrantFiled: March 20, 1990Date of Patent: June 4, 1991Assignee: Hoechst AktiengesellschaftInventor: Holger M. Buch
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Patent number: 5010180Abstract: Water-soluble azo compounds corresponding to the general formula D--N.dbd.N--K which have advantageous fiber-reactive dyestuff properties and dye materials containing carboxamide groups and in particular materials containing hydroxy groups, such as wool and in particular cellulose fiber materials, in deep fast shades are described.In the formula D--N.dbd.N--K:D is a radical of the general formula ##STR1## in which Y is the vinyl group or an ethyl group in the .beta.Type: GrantFiled: February 1, 1990Date of Patent: April 23, 1991Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Uwe Reiher
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Patent number: 5006645Abstract: Dyes of the formula ##STR1## wherein K is the radical of a coupling component which can additionally contain azo groups, R is hydrogen or methyl, and Z is a fluorine atom, a substituted or unsubstituted amino group, a substituted or unsubstituted hydroxyl group, a substituted or unsubstituted mercapto group, or a substituted or unsubstituted hydrocarbon radical are distinguished by high reactivity and they produce dyeings of good wet- and light-fastness properties. The dyes of the Formula (I) are suitable for dyeing and printing a very wide variety of materials, such as silk, leather, wool, polyamide and polyurethane fibres, and especially cellulosic materials of fibrous structure, such as liner, cellulose, regenerated cellulose, and in particular cotton. They are suitable both for the exhaust method and for dyeing by the pad-dyeing process. They are also suitable for printing, in particular on cotton.Type: GrantFiled: September 14, 1989Date of Patent: April 9, 1991Assignee: Ciba-Geigy CorporationInventor: Karl Seitz